What Is It With Guys Over 39?

Is that the magic age when women of their own era become invisible or inherently undesirable because we might show a few lines, or signs of childbirth, or maybe because we might be wise to the mid-life male and their foibles and flaws?

Dating statistics in the western world consistently bear out the trend for older men to prefer women a decade or two younger, whereas women (apparently – not me) prefer men in their own age group when dating.

What is not clear from the data is what women were seeking when they ticked that box. Perhaps it was long-term compatibility or companionship rather than excitement, passion and to revive their forgotten sexual capacity.

After all, if a woman is dating again in her forties it’s highly likely that she endured a long period of monogamy during which (again, if the data can be believed) she probably didn’t often get her needs met. Combined with the questionable state of sexual reciprocity in marriage, if the relationship was suffering the agonising slow decline, the chances are that sex was off the agenda anyway.

However, the point I am making here is that – for whatever reason and on average – older men do not seek out their female counterparts in the online dating world.

This is pretty depressing for a woman in midlife, who holds out hope for a mutual and satisfying partnership at some stage during this second half of life. The fact that I can and do attract the young things without even trying is beside the point, because the basic maths shows that a 10 or 20 year age difference is just not sustainable. That was a major factor for me when I chose to end a two-year intimate relationship with my then 27-year-old lover.

Let me illustrate this point by sharing my experiences and perceptions across three dates from this weekend.

After a five-month absence from dating, chatting, texting, swiping and putting my profile out there, I dipped my toe back into the (cess)pool that is online dating. Oh so many bites; I narrowed them down to a dozen and arranged dates with three, based on random selection and even more random timing. There was precious little analysis and it was very quick, because I rarely know how my free time might pan out and when I might be able to claw a couple of hours away from my 24/7 teens.

I chose two guys of roughly my vintage plus a latecomer who burst onto the scene and wowed me with his erotic storytelling and our instant connection via kik messaging.

The 50-year-olds were unremarkable and if I squinted and blurred my vision I could imagine them perhaps being attractive to my tastes.

I withheld judgement, prayed for the best and arranged to see one for a couple of hours on a Friday evening, and the other for the Sunday early afternoon.

I’d been chatting to Mr Sunday afternoon all week and thus far found conversation yawn-worthy and unremarkable. Mr Friday night, on the other hand, surprised me with his eager texting and I propositioned him for the date, knowing all too well that meeting as soon as possible was best. He was very keen and reliable and we met the next night at a local upmarket hotel.

I was standing at the bar when he sidled over to me and said a mild hello. He may have kissed my cheek. We made polite conversation while ordering drinks (we paid separately) and then found a booth in the quiet lounge room of the hotel. Conversation was easy and smooth and I didn’t have to work too hard – one benefit with dating older men is that they usually know better than the young ones how to maintain the conversational flow.

Topics were pretty tame and he sat miles away across the table, with no attempt to move closer to me or initiate any sort of physical contact. We talked casually for almost two hours, covering topics centred around him and his life, although he paid lip service to me a few times. It was pleasant but as I surreptitiously studied him I couldn’t imagine having sex with him, or that he’d ever be in the grip of passion or emotion. He had thin lips and that’s an instant turn off for me.

I suggested that it was time to leave and we meandered out to our cars. As we said goodbye I felt a surge of unexpected warmth and the next thing I knew, we were kissing. I don’t think I initiated it, but I didn’t recoil because he was actually a pretty decent kisser. In my mind I thought I’d give him a go and see whether he might have potential in bed, seeing as how that was the point of our meeting – to find a lover/FWB/FB (whatever term you prefer).

It was quite a long kiss and it did involve tongues. It wasn’t unpleasant but nor did it trigger any desire to go further, and certainly not to touch him elsewhere. Fortunately he was retrained and didn’t grope my breasts or arse, but he did steer me towards my car and kissed me again in relative privacy. We said goodbye a few minutes later and as I drove home I thought I’d just wait and see what happened next.

We texted a little later that night. “It’s funny what happened when I kissed you,” he messaged. “Didn’t you notice my erection?” Actually I hadn’t and it seemed sort of crass to mention it. Oops, I’m showing my prejudices because I just can’t seem to get excited by lukewarm old farts who consider lawn bowls a suitable topic of conversation on a date.

We had a bit of back and forth banter, and for some reason I agreed to send him a boobiepic (full nipples and all) since he asked. In hindsight, he didn’t so much as ask as demand, which should have been a warning. I pondered and sent him my best, guaranteed-to-produce-oohs-and-ahs full frontal shot.

Now the ex-young lover had a breast fetish so I have quite a few of these in my collection, but even if I do say so myself, this shot is pretty amazing. I am honored to have such boobs, and I really have a surgeon to thank for it since I had a breast reduction operation seven years ago. However, I don’t usually reveal that! So you’ll understand my disappointment when Mr Friday night barely hesitated before texting, “good – very good.”

Fuck you, I felt like saying. Where’s the moans and exclamations and all the hoohar – or is it only the young ones who know how to appreciate a lady’s assets?! It’s not like I didn’t say all the right things when he showed me his saggy man-boobs and graying chest hair.

I had to work late (the joys of freelancing – no, I mean it!) and so at about midnight I stopped in at the site we met to see how my message box was coping with the onslaught. I was still fresh meat and I’d already figured out that real women were in the minority – hence the bulging inbox and multiple propositions. I spent a short time moving some guys over to kik and deleting others, then I went to bed thinking nothing of it.

The next morning, while lounging in bed making up for my late night’s work, I checked into the site again and found a message from Mr Friday evening date. “I saw you were on here tonight,” he said. I casually replied that I had been, and was that a problem?

To be honest, I haven’t logged on to the site since then (the reasons why will soon become clear) but on our kik account my message remained unread for two whole days.* I haven’t heard from Mr Friday night since so I guess he did object to me logging onto the site! We hadn’t even arranged a second date, discussed anything personal and already he wants to control me?! Phew, lucky escape!

Onto second date for the weekend, Mr Sunday afternoon. Also about 50, he was a different type of guy – workaholic, self-obsessed, a nervous babbler and someone so out of touch with his emotions I couldn’t even imagine being in a bedroom with him, let alone having actual sex. We had gelati and coffee (he paid, though somewhat reluctantly, but I let him go through with the offer) and over almost two hours, in his mildly high-pitched voice, he talked incessantly about himself, his hobbies, his children, his ex-wife, his property developments, his study – including his forthcoming assignments – and his love of classic cars and motorbikes.

I was friendly enough because I had a get-away plan and I soon calculated that date #3 held the most potential (young hottie).

Boy was I correct and I extricated myself from Mr Sunday afternoon as soon as possible. So utterly unsexual was he that he couldn’t even manage a peck on the cheek and we hugged instead.

I drove the five minutes to my third date for the weekend, Mr Mid-30s Hottie, who’d been texting me while he waited three hours for me to arrive at our destination. He’d been on a cycling event and rather than drive all the way home, he decided to wait for when I’d be free at 3pm. Sweet – and keen!

“Why don’t you meet me at my car so I can give you a proper welcome kiss?” he messaged on kik just as I was at the traffic lights. I couldn’t figure out where he was parked, so we met at my car instead – true to his word, he grinned and complimented my appearance and then embraced me in a passionate kiss. Now that’s how to make a good impression – especially with a sex-starved cougar who’s had to endure two boring old farts for more than four hours of blathering!

And he was drop-dead gorgeous, did I mention that?!

At least 6ft5, fit and lean, black plastic glasses (just like the pic!) and a nerdy shyboy appeal that hits the right spot for me every time! (I have an internal warning – but he doesn’t sound the alarms because, when it comes to sex, he is voracious and completely self-assured.) We giggled, held hands (while I felt up his arse and he laughed) and walked to the café.

As requested, I was wearing a revealing top and as he sat opposite me I could feel his eyes drinking me in. We made pleasant conversation (yes, it was harder work that the older guys because Mr Mid-30s Hottie is socially awkward,) covering a lot of topics. About an hour later he suggested we should go out to the car. I agreed and we walked hand in hand, with some more arse fondling, to my front seat.

It was broad daylight, sadly, and as neither of us are into dogging (having sex in public – it’s a thing!), we kept it fairly tame though he was very keen to escalate, but gentleman enough not to push it. However, two things were immediately clear – firstly, I really liked him and found him deliciously attractive, and secondly, he found me sexy, hot, desirable and worthy of a second date!

He has this irresistible combination of self-doubt, awkwardness and shyness – but combined with a sexual confidence and the body of a god! And he’s a fabulous kisser – I definitely wanted more of that but was finding the whole kissing in the front seat of a car thing uncomfortable, and there were too many people milling about outside.

So here are my thoughts on the whole age thing – the difference between guys and girls as we age.

I think Lauren is spot on when she says that men tend to get old quickly and set in their ways. They are also less likely to look after themselves and stay attractive. (Blunt I know, but that’s just a comment about their packaging – here’s what’s really important).

On the inside, however, is where the real difference lies – women in their second phase are often highly sexual, passionate and excited to be alive. Men, on the other hand, are often withered, bitter and cynical.

Take Mr Friday and my tits – he may not have seen better in his life (unless they were on a porn star) and yet he could barely raise a compliment and then ghosted me because he was hurt/angry/jealous, [delete whatever is not applicable] because I checked into the site where we both met, after I met him! And let’s not forget that HE checked into the site too!

I have found men my own age to be highly critical of a woman’s body – even sporting their own pot bellies, double chins and craggy lines, they expect youthful perfection in their potential partner. Men of my generation also seem unable to flirt or playfully engage on a level that is mischievous or ambiguous.

I hear this often from other women, and I’m not sure why or whether it’s universal. I guess I should qualify that statement by clarifying that I’m talking here about men on dating sites, or single men looking for something (sex, a partner, whatever).

Most young guys assume that, when you say you like younger men, that it’s all about the sex – that they’re obviously better, more lustful and with greater stamina because they’re young.

I haven’t found that to be the case, although Christine Feminist probably disagrees. She’s had some amazing sexual experiences with young guys, but sadly most of mine have been duds. Being a porn-fucked Millennial is really common! The symptoms are obvious when you’ve been in a long-term relationship and you know how normal men function. I’ll write about it another time. So for whatever reason (region-based, age-based, my bad luck or bad timing), most of the 30-plus sexual experiences I’ve shared with guys under 35 have been abysmal. I’ll be sharing those stories in future so stay tuned!

The important point here, however, is that it’s not the sex that makes younger guys so appealing – it’s the attitude! It’s the fun and the flirting! It’s the passion, the feels! It may not last – but it lights my fire that’s for sure.

As for Mr Mid-30s Hottie, he and I have barely stopped texting erotic tales, flirtatious and rambunctious desires and madly arranging our first all-day date coming up in two days! I can barely wait and the best part is that neither can he.

Time will tell whether he is as amazing in bed as he seems, but thank the goddess I don’t have to wait much longer to find out. Watch this space!

* I checked onto the site a week later and all evidence of Mr Friday night was removed! My guess is that, in a sulk, he packed up and left!

Wow you are a man after my own heart in more ways than one – your drawings are divine and I especially love the capsicums as I have a thing for drawing and painting them! I look forward to reading more of your blog now that I am a follower!

Wow, I am starting to feel this way myself. When I first got my divorce, I couldn’t imagine dating someone much younger but the more I date, the more I find myself attracted to the younger men. I just turned fifty and have men in their 20’s hit on me and flirt with me all the time. I have found the younger men are more fun and do have more energy. They also tend to look much nicer. You describe the differences perfectly. I am trying to enjoy my life now and if that means younger men, then so be it. I do not want to be BORED

You always put it so eloquently. I’ve noticed that, speaking generally, women tend to expand as they get older and men tend to narrow. I think it’s because women traditionally have spent the first part of their lives pleasing and caring for others, and getting older for us is a process of removing the layers of conditioning to discover our core selves. Traditionally, men are socialised to be their full selves from a young age and to have others cater to their needs, so for them ageing becomes a process of losing things (the women looking after them, eventually their jobs, which they so often define themselves by) etc. Also, women are more comfortable exploring emotions, whereas men are taught to bury them. A massive generalisation and over-simplification, of course. But too often older men on dating sites are looking for someone to fill the hole left by their ex-wife without taking time to really open their hearts up and rediscover themselves. Interesting to see how the next generation will manage all of this, as traditional gender roles become less and less defined. x

Brilliantly and tactfully explained, as always! This is a very good short description of what I might have said myself if I had taken the time to explore my thoughts further. Thank you for following Unleashing the Cougar!

I loved your post! It kept me engaged and interested for more. I do disagree with some things as I am 24 and my boyfriend of quite sometime is 53. I will say that MOST 50 something year old men do sport belly’s, lazy, passionless, and have lost their lust for life, but not all…*cough cough* like my boyfriend LOL. I do have a blog of my own that dives into my experience dating a man nearly 30 years older than me so It’s fun to read about different and “out of the norm” relationships and life experiences like yours.

Thanks! I’m glad you found it interesting and I am going to head straight over to yours because I find that fascinating. By the way, my current heart connection/lover is 56 and I have to say he most definitely doesn’t fit that group of ‘types’ either. In fact, he’s so sexy I can’t keep my hands off him!